This qualitative study examines how workplace socialization can be addressed through a newcomer’s linguistic practice in chitchat on Facebook status updates. Based on Wenger’s (1998) framework of Communities of Practice and Gee’s (2011) model of discourse analysis, it investigates over 60 status updates made by a new employee and his colleagues spread over five months. Results suggest that the newcomer chitchats with his colleagues in three arbitrary manners, and that he irregularly moves back and forth to the integrated membership. Sometimes he highlights the newcomer status through chitchat, while in other times he behaves like a core member in the community. However, the majority of his practice fall into a relatively moderate range between the new and the integral. Behind his participation in chitchat is the characteristic psyche and behavior during socialization into the workplace. A model of language and communication in workplace socialization is further suggested upon an in-depth elaboration on the data analysis. It is concluded that chitchatting in status updates can function as the gateway to understand workplace socialization. More studies are needed to explore how workplace socialization can be addressed through other speech events in computer-mediated environments.